Aliphatic amines produced with beef tallow, coconut oil, palm oil, and the like are important intermediates for domestic and industrial applications. Aliphatic tertiary amines have a wide variety of applications such as a fabric softener, an antistatic agent, a rinsing agent, and other detergent through modification into a quaternary ammonium salt, an amphoteric surfactant, or the like.
Arts of production of a tertiary amine, in particular a method for efficiently producing a tertiary amine, have been explored by the process of reacting an alcohol and a primary or secondary amine in the presence of a catalyst.
JP-A 2008-94800 discloses use of a film catalyst containing a catalyst metal and a film supporting the catalyst metal on the surface thereof. The method does not have to stir or separate the catalyst by filtration, compared with a reaction in an alcohol containing a powder catalyst dispersed therein. JP-A 2008-94800 describes that reactive gas is supplied to a reactor through a feed opening having a diameter D of 0.3 to 200 mm.
JP-A 61-291044, published on 1986, discloses a method for facilitating mass transfer and heat exchange by constructing each honeycomb catalyst layer with a honeycomb catalyst and a static mixing element inserted in the catalyst. The static mixing element is expected to facilitate mixing of gas and liquid between honeycomb catalyst layers.
However, as described in Koei Kawakami et al., Kagaku Kougaku Ronbunshu (Collection of Chemical Engineering Papers) 13 (1987) 318; Patrick, R. H. et al., AIChE. J. 41 (1995) 649; Thulasidas, T. C. et al., Chem. Eng. Sci. 54 (1999) 61; and Sederman, A. J. et al., Catal. Today 128 (2007) 3, in case of conducting a reaction between gas and liquid flowing upward in parallel through a monolith catalyst in a reaction column, a residence time distribution in the reaction column is same to that in a complete mixing reaction system. A part of flowing gas and liquid may take a short pass, and another part may remain in the reaction column for a long time, causing an overreaction. It is also described that the residence time distribution cannot be improved from the state same to a complete mixing reaction system just by increasing a gas dispersibility.
US-A 2008/0004472 discloses production of a tertiary amine by reacting an alcohol and a primary or secondary amine in the presence of a film catalyst. JP-A 10-118473, published on 1998, and JP-A 10-146523, published on 1998, disclose a gas-liquid dispersion device generating a gas-liquid distribution phase.